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22 Things to Do in Pittsburgh This Week · June 18–21, 2026

Top Picks This Week

Disco Drag Brunch at Velum Fermentation

A disco Pride Month drag brunch with performances, doors at 11 AM and showtime at noon, at Velum Fermentation in the South Side.

Passion Pit – The Pretty Penny Tour

Passion Pit brings their indie-pop sound to Stage AE indoors on Monday night with support from Arden Jones, presented by 91.3 WYEP.

Summer Alfresco Wine Dinners at The Priory Hotel

Intimate outdoor wine dinners under the stars featuring four Spanish wines paired with four chef-crafted tapas and live music at The Priory Hotel.

Festivals & Special Events
Juneteenth Boat Party on the Gateway Clipper
An all-Black boat party on the Gateway Clipper celebrating Juneteenth on Pittsburgh's rivers.
Thursday, June 18, 2026 · Gateway Clipper, South Shore
Pittsburgh CityPodcast / City Cast PittsburghCalShare
WPA Juneteenth Celebration at Point State Park
Western Pennsylvania's official Juneteenth celebration at Point State Park with live events and community festivities.
Friday, June 19, 2026 · Point State Park, Downtown
Visit PittsburghCalShare
Millvale Pride Drag Brunch at Strange Roots
Celebrate Millvale Pride Day with a fierce drag brunch at Strange Roots Experimental Ales in Millvale.
Saturday, June 20, 2026 · Strange Roots Experimental Ales, Millvale, PA
@ssproductionspghCalShare
Squirrel Hill Night Market
Massive night market on Murray Ave featuring 100+ local artists, small businesses, live music, food trucks, and community festivities, 6–10 PM.
Saturday, June 27, 2026 6:00 PM · 1839 Murray Ave, Pittsburgh (Squirrel Hill)
I Made It! MarketCalShare
Arts & Culture
One Mo' Gain: 30 Years of Cave Canem
A free poetry and visual arts event at the August Wilson Cultural Center celebrating 30 years of Cave Canem.
Thursday, June 18, 2026 · August Wilson Cultural Center, Downtown
Pittsburgh Cultural District – Trust Arts CalendarCalShare
Outdoors & Active
Blacksmithing Basics at Carrie Blast Furnaces
Learn hands-on blacksmithing basics at the historic Carrie Blast Furnaces in Rankin.
Thursday, June 18, 2026 · Carrie Blast Furnaces, Rankin
Pittsburgh CityPodcast / City Cast PittsburghCalShare
City of Bridges Run Club – Monday Oval Workout
Coach Kim leads a weekly evening track workout at Schenley Oval — open to all runners.
Monday, June 22, 2026 · Schenley Oval, Pittsburgh
@cityofbridgesrunclubCalShare
Schenley Park Fest
A casual park day with food trucks, lawn games, picnic blankets, and community fun at Schenley Park Overlook, 3–6 PM.
Saturday, June 27, 2026 3:00 PM · Schenley Park Overlook, Pittsburgh
@pghsocialclubCalShare
Music & Nightlife
Savannah Dexter at Jergels Rhythm Grille
Country artist Savannah Dexter performs live at Jergels Rhythm Grille tonight.
Thursday, June 18, 2026 · Jergels Rhythm Grille, Warrendale
Drusky EntertainmentCalShare
Drag Bingo at Eleventh Hour Brewing
Pride Drag Bingo night at Eleventh Hour Brewing with six games of bingo and a fabulous drag show, bingo kicks off around 7 PM.
Saturday, June 20, 2026 7:00 PM · Eleventh Hour Brewing, Pittsburgh
@ssproductionspghCalShare
Passion Pit – The Pretty Penny Tour
Passion Pit brings their indie-pop sound to Stage AE indoors on Monday night with support from Arden Jones, presented by 91.3 WYEP.
Monday, June 22, 2026 7:00 PM · Stage AE, Pittsburgh
Stage AE / PromoWestCalShare
Brake Run Album Release w/ Sgt. Hare Apollo and A Cute Angel
Local shoegazers Brake Run celebrate their new album at The Government Center with Columbus alt-rockers and sweet openers.
Thursday, June 25, 2026 8:00 PM · The Government Center, Pittsburgh
@arcane.cityCalShare
An Evening With Joe Grushecky and the Houserockers
Pittsburgh rock legend Joe Grushecky and the Houserockers take the intimate City Winery stage for a special evening.
Friday, June 26, 2026 · City Winery Pittsburgh, Strip District
City Winery PittsburghCalShare
Free Events
Juneteenth in the Square – Market Square
Free Juneteenth community celebration in Market Square with live programming and vendors running through June 21.
Friday, June 19, 2026 · Market Square, Downtown
Visit PittsburghCalShare
Dance & Fitness Classes with Pittsburgh Ballet Theatre
Free outdoor dance and fitness classes with Pittsburgh Ballet Theatre at Arts Landing, running Saturdays through September.
Saturday, June 20, 2026 · Arts Landing, Pittsburgh Cultural District
Pittsburgh Cultural District – Trust Arts CalendarCalShare
Kendra Gives Back Shopping Event
In-store shopping event at Kendra Scott in Shadyside with light sips and sweets; 20% of purchases benefit Open Up Pittsburgh.
Saturday, June 20, 2026 1:00 PM · Kendra Scott, Shadyside
@openuppghCalShare
Free Concert at Hazelwood Green – Son Rompepera & El Montenegro
Free outdoor concert at Hazelwood Green featuring Son Rompepera, El Montenegro, and special guests, with food trucks and breweries, all ages.
Sunday, June 21, 2026 · Hazelwood Green, Pittsburgh
@secretplanetpghCalShare
Food & Drink
Disco Drag Brunch at Velum Fermentation
A disco Pride Month drag brunch with performances, doors at 11 AM and showtime at noon, at Velum Fermentation in the South Side.
Saturday, June 20, 2026 11:00 AM · Velum Fermentation, 2120 Jane St, Pittsburgh
@ssproductionspghCalShare
Family-Friendly
Cinema in the Park – 'Creed' at Grandview Park
Free outdoor screening of 'Creed' (PG-13) at Grandview Park Bandstand as part of Dollar Bank Cinema in the Park.
Saturday, June 20, 2026 · Grandview Park Bandstand, Pittsburgh
@pgheventsofficeCalShare
I Made It! Market at The Waterfront
Outdoor artisan market featuring over 35 local artists and food vendors at The Waterfront in Homestead.
Saturday, June 20, 2026 11:00 AM · 100 West Bridge Street, West Homestead
I Made It! MarketCalShare
Date Night
Summer Alfresco Wine Dinners at The Priory Hotel
Intimate outdoor wine dinners under the stars featuring four Spanish wines paired with four chef-crafted tapas and live music at The Priory Hotel.
Friday, June 19, 2026 · The Priory Hotel, Pittsburgh
@stufftodoinpittsburghCalShare
Pittsburgh SUMMER LOCK & KEY SINGLES PARTY
A fun singles mixer at Ruckus Cafe where guests exchange lock and key charms to meet new people, ages 29–59.
Saturday, June 27, 2026 7:00 PM · Ruckus Cafe, Pittsburgh
Eventbrite PittsburghCalShare